Most Wonderful Time of the Year
by SloaneRisette
Summary: At the end of a rough semester, the girls of Blackwell Academy decide the best way to finish it is with a Secret Santa. And while struggling with a crush she's sure will amount to nothing, Max is dedicated to thinking up the best gift possible.
1. The Most Stressful Time of the Year

**This will be my little Christmas-y fic for the month! It's a short, two chapter thing, it's already done but I'll space it out a bit more, and will probably upload the second chapter later this week. I've been really interested in writing Max/Dana because I find the idea behind the pairing just really interesting in general? I'll probably do more with them in the future. Hope you all like it! I had a lot of fun writing this.**

* * *

It was mid-morning, December 1st. The girls of Blackwell Academy had all gathered in the hall of the dorm building that Sunday morning, to prepare for the first of their many holiday activities. After October, after what had happened with Kate, all of the girls had made an unspoken pact to be kinder, get closer, and appreciate each other more. And it had all been working out incredibly well. In a few weeks, Victoria, Taylor, and Courtney had all been treating Kate, Max, Alyssa, everyone kinder than they ever had before. Everyone was nicer.

It wasn't all perfect— there was still the occasional fight, someone taking too long in the shower, small things like that. But it relieved Max that things were going well— she wasn't ever really sure it would end up like this.

So there they were, all ten of them, standing around each other: Max, Kate, Victoria, Alyssa, Stella, Courtney, Dana, Juliet, Taylor, and Brooke. Victoria was holding a small bowl filled with folded up pieces of paper.

The girls had all decided on doing a little gift exchange. They figured it would all be a great way to bond with each other and show how much they all cared. Plus with finals around the corner, working on getting someone a gift would be all nice and fun and a good way to relax amidst the stress of studying.

That's how Max saw it, at least.

"Ok everyone, you pick a piece of paper from the bowl, and as long as it's not yourself, you keep it, and that's the person you get a gift for," Victoria explained.

"And you have to make sure it's heartfelt and meaningful. Don't just find something expensive and get the person that," Alyssa said. There was a nod and murmur of agreement from the group. With any luck, Max would get Kate. She knew everything that Kate loved, so figuring out a heartfelt, meaningful gift would be easy.

But of course, there was one other person Max was hoping she would get— crossing her fingers for, even.

And that was one Dana Ward, head cheerleader at Blackwell Academy. She was cool and beautiful. She could be a model if she wanted to.

She was the girl that Max had been awkwardly crushing on like mad ever since she saw her at cheer practice for the first time. She had been coming back to her dorm after an afternoon of taking some nature pictures. She saw the brunette leading the team on a new routine for a big game at the end of the week, and she was so amazing. Gorgeous, athletic, and kind.

Gorgeous and athletic were two things Max definitely wasn't.

When Max came out to Kate a few weeks later, she told her that she was crushing on Dana— hard. Kate had been so supportive, even if she did admit that it seemed obvious to her.

But as much as Kate assured her things would work out— that Dana would _**definitely**_ react well if Max had ever told her how she felt— Max knew that wouldn't be the case.

Not only was she leagues cooler than Max, she was dating Trevor. It made the whole thing impossible. How could she tell her crush how she felt when she was dating someone? Let alone if she even was bisexual?

Nope, no way. She was going to have to stay quiet on this, even if it did suck.

And it _**did**_ suck.

"Max? Max!" came the voice of Juliet, Dana's best friend as Max was suddenly snapped out of her thoughts, the bowl being handed to her by Taylor.

"Sorry…" she mumbled, now bright red, as she took the bowl and started to shuffle her hand through it.

 _"Good job, Max… even after everything you've done you still space out like an idiot…"_

After a few more moments, she finally pulled a piece of paper out and then handed the bowl to Kate.

 _"Please get Kate, please get Kate…"_ she prayed to herself as she unfolded the paper, seeing the name on it.

Of course.

Dana.

It figured that Max would get the one person she wanted as much as she didn't.

 _ **Great.**_

What would she even get her? What would Dana want most? What did she not have already?

She had a few weeks to figure it all out, but she knew this wasn't going to be easy.

Max's eyes lazily followed as the bowl passed from Kate to the last few girls, and then back to Victoria.

"Ok then, everyone has their secret Santa! When you have your gift ready you can place it under the tree when we set that up, or keep it to hold on to until we exchange gifts," Courtney said, hands clasped together, smile on her face.

"Yeah, just remember, we're exchanging gifts after the last finals, on the twentieth! So be here in the evening!" Taylor added.

"We'll be doing the tree decorating this Friday, so if you want to participate, make sure you're there for that! Finals are coming up and everything is due, so if you really can't make it, don't worry, but if you can, it'll just be a few hours. We'll have Christmas music and tea and cocoa for everyone!" Kate said excitedly. Her energy couldn't help but make Max smile, even when she was stressed out.

The crowd of girls started to disperse, all off to go about their Sunday plans, while Max quickly grabbed Kate's arm.

"Kate, you're not busy, are you?" she asked, starting to drag Kate to her room. Kate's eyes widened at the sudden surprise.

"What? Oh— no! Max— is everything ok?" she asked, concerned at the sudden panic her friend was showing.

Max led Kate into her room and then followed behind, shutting the door. As Kate sat on Max's bed, Max just about collapsed on the floor, arms spread out, staring at the ceiling, letting out a sigh.

"Max… what's wrong?"

"I got Dana."

Kate's look of worry turned to a wide smile.

"That's so great Max! What are you going to do for her?"

"That's the problem, Kate! I don't know yet! I was hoping I'd get you because I know what I'd get you in an instant… but I'm at a loss for her," she said, another sigh escaping her lips.

"Aww, Max. If you need help, I'll be here to help you figure it out. We'll make sure you get Dana the best Christmas gift she could ever want," Kate assured her.

"Thanks, Kate. You have no clue how much I appreciate it," Max said to her friend, looking over at her. She was real glad she came out to Kate about this, else she would be stuck at square one the next two weeks.

"…So who did you get?"

Max felt bad asking, but she always was curious.

"I got Alyssa. I'm not entirely sure what I'll get her yet, but I have a few ideas," Kate said, small smile on her face, pleased with everything. She got one of her friends in the gift exchange, and Max got her crush. It was a win-win in her mind.

"I wish I had ideas in mind…" Max groaned.

"Come on Max, don't worry. We'll think of something soon," she said, hoping to cheer the brunette up.

"You and me are still going to exchange gifts, right?" Kate asked, tilting her head curiously at her best friend.

Max now pushed herself up, sitting cross-legged, smiling at Kate.

"Of course! I… already kind of ordered something for you and it'll be here soon," Max admitted, a bit red. As soon as Thanksgiving was over, she had been searching for gifts for Chloe and Kate, and while she hadn't found something for Chloe yet, she found something for Kate right away and ordered it as soon as she could— a little tea set. Nice and brand new and the style was _so_ Kate.

"Oh, gosh Max. I'll get you something soon so we can exchange before the break."

"Don't worry if you can't, Kate. I just really wanted to get you something nice. You're one of my best friends, you deserve a great Christmas gift."

"You too, Max. You've done so much for me, and even discounting that, you're one of the best people I've ever known. I promise I'll get you something great," Kate told her. Max got up and headed over to the bed, sitting next to the blonde and pulling her into a hug. Kate hugged back.

After a few moments in silence, the two finally pulled away.

"Now, we have a mission to start. We need to figure out the greatest possible gift Max Caulfield can get for Dana," Kate smiled.

Max smiled back.

Maybe they'd be able to figure out something worthwhile after all?

The two sat for a while, tossing ideas back and forth aimlessly, though nothing seemed to stick with Max. A CD of her favorite songs, a grouping of movies she loved so she could watch while studying, a new outfit that she heard her talk about with Juliet and Trevor…

But none of them sounded great. They were just average ideas— something you'd do for a friend when you had the time or the money, nothing _that_ special.

"Max, you're so stupid, you can't even think of anything!" she groaned out angrily, now lying on her bed an hour and a half later. Kate was sitting next to her, and put a reassuring hand on Max's shoulder, patting it gently.

"Don't beat yourself up, Max. We only just found out who we're going to be giving gifts to. I don't think anyone has figured out what they're getting yet."

Max sighed, which left Kate frowning.

"I know Kate, just—" she started, pushing herself up and folding her legs, looking at her best friend who was looking intently and curiously at Max.

"I really like her. You know that. I want her… I want her to open her gift and think about how it's the greatest gift she could have ever gotten this year— or ever!" Max told her, exasperated. Kate nodded.

"I get that, Max. Just… please don't beat yourself up?" Kate asked, and Max nodded.

"Ok… ok…" she said.

It was a few more moments, before Max stood up, eyes wide.

"Kate I think I just thought of the best idea ever," Max told her, now smiling widely, turning to look at Kate.

"What is it?"

"Ok, so, what if I took a bunch of pictures of her at cheer practice and at games when she's doing all great and at all sorts of events and I put them all together in like, a scrapbook? So she can see all her best moments— and— and I can decorate it, and—"

"Max, that's such a wonderful idea. She'll just love it— and it'll be easy to do because that's just what you do," Kate said excitedly.

"I… well, I already have taken a few pictures of her and the squad during practice, so at least I have a bit of a head start," she said, still smiling.

It was the perfect idea. Dana was sure to love it.

…At least, Max hoped so

"You know, this means you'll have to get some school spirit now and go to the games, right Max?" Kate giggled, and Max turned red.

"Yeah… and now it's cold, this is gonna suck," she sighed.

"Don't worry Max, I'm sure how much you like her and seeing her cheer will help make it easier," Kate teased.

"Thanks Kate," Max said, wrapping her arms around her friend. Kate hugged back.

"Anytime, Max. You know I'm always here for you," Kate assured her, the two letting go.

"I think I'll get going now, I still need to start working on a paper for Friday. Make sure you don't daydream about Dana too much, Max," Kate teased as she started to head to the door. Max sighed quietly, closing her eyes.

"Yeah, homework…" she sighed. How could she even focus on homework when she had a gift to work on for her crush!?

"I'll see you later Max. Let me know if you need any help," Kate said as she opened the door and waved goodbye. Max waved back.

"Thanks Kate, let me know if you need anything either!" she said as Kate closed the door behind her, as Max turned over to look at the mess of Polaroids she had scattered on her couch.

"Ok, Max. You have a few weeks to make the greatest scrapbook for Dana," she said, taking a deep breath.

She could do it.


	2. Your Secret Santa

**End of this short little fic! Hope you all like it! Just a little fun Christmas/holiday thing trying out a new pairing I've been interested in for a long time but haven't done anything with.**

* * *

It had been a busy couple of weeks. Finals were now done, and somehow Max had managed to survive them. As far as she knew, she didn't fail any of her finals or projects, but the thing she had been focused on that whole time was Dana's gift.

That Sunday afternoon, as soon as Kate had left, Max had been putting together photos she had taken when she had gone to watch cheer practices, the school's Halloween party, and even at fun dormitory hangouts that all of the girls had been having. Even when Dana had posed in Max's photography class, she snuck in a few shots. It was about twenty pages, small little thing, with pages decorated to reflect the things Dana loved— mainly gleaned from what she had heard in classes or in the hallways, or seen in decorations from her dorm room.

It was perfect. Max had spent hours on this. She wanted a perfect little scrapbook for the girl she was crushing on. The normally shy, down on herself wallflower was confident for once. She had finished putting the wrapped scrapbook in a cute, Christmas-y bag with decorative red and green Christmas paper.

…Ok, it was a bit of a mess. The decorative paper was all crumpled and messed up— and she had to use way too much tape to wrap her gift, but it was the thought that counted, right? After all, Dana would unwrap it and wouldn't even care about the packaging after, right?

Right?

"Max, there's no time to be nervous about this. It's the thought that counts."

With a deep breath, she picked up the bag and headed for the door, already able to hear most of the girls talking to each other out in the hall. This wasn't a competition of who got the better gift for their Secret Santa, it was just to do something sweet for someone for the holidays.

"Everything is going to be fine," she said under her breath. She opened up the door to see Courtney and Taylor talking to Kate, who was wearing an adorably bad Christmas sweater. Down the hall by the tree was Juliet, Victoria, and of course, Dana. Max gulped hard, already feeling her mouth drying— she could feel herself turning red. She felt like she was starting to sweat because of how nervous she was.

Stella, Brooke, and Alyssa were heading down from the other end of the hall. She was nervous, but Max knew she could do it. It was just giving a gift.

She just had to remember that.

Waving to Kate and the other girls around, Max put her gift down as stealthily as she could, turning the tag around so "FOR DANA" could be seen easier. She backed away slowly, hoping she wasn't obviously seen as placing Dana's gift— that she was just looking at all the cutely wrapped gifts.

God, she did a really bad job on her wrapping in comparison…

Max took a deep breath and walked over to Kate, now wringing her hands.

"Are you excited to see what you got?" Max asked Kate, still looking over at the tree.

"Yeah, but I'm mostly hoping Alyssa likes what I got her," Kate said, smiling. Max nodded.

"I know she will, Kate. You put a lot of work into getting that all together. She'll love it," Max assured her, placing a hand on her shoulder. Kate smiled.

"You always know what to say, Max."

"I just hope she likes my gift…" Max sighed. Now it was Kate's turn to help her best friend feel better.

"Max, I know this isn't easy for you, but anyone would appreciate the work you put in for them. I looked through every page of it at least five times with you. It's perfect," Kate told her. Kate was amazing at reassuring Max, but she still had that twinge of anxiety.

"Thanks," she said simply, hugging the blonde. She just had to remember that everything would be fine.

Victoria coolly walked over to the front of the tree, putting her hands together.

"First, congrats on everyone making it through finals," she started, and the group of girls all cheered, congratulating each other quickly.

The past week had been many sleepless nights and cups of coffees out in the hallways that were lit softly by laptop screens. Tuesday night Max had been working on putting the finishing touches on Dana's gift, and then spent the next three hours— until about two in the morning— studying in the hall with Victoria and Juliet for a science test.

To say that the girls of Blackwell had a rough week was an understatement.

"Next, we all have some gorgeous gifts under the tree, and I'm really glad everyone participated in this," she added.

"So, everyone, you can go get your gifts and start opening! You can always let the person know you got the gift for them If you want!" Courtney called out, and the girls started to head over to the tree, searching through for their gifts. Each one handing over a gift for someone else if they found it.

"Max! Here's yours," a voice called, snapping Max out of her distraction of the worst case scenarios going through her head. She looked down to see Dana handing a present to her.

"Oh— thanks, Dana…" she mumbled, turning a bit red as she took the box and started to unwrap it. She opened up the box to see a pink, knitted sweater, with a beautiful and adorable deer design on it.

"This is so beautiful," she said, smiling wide. For a brief moment she was distracted from the worries she had the past few weeks. The purple-haired Courtney came traipsing over to Max, smiling wide.

"You like it?" she asked, and Max looked up at her.

"You got this for me?" Max asked, and Courtney nodded.

"Yes I did! I saw a girl online who sells custom sweaters and I know how much you love that hipster look and deer so I thought it would be _perfect_ for you."

Max pulled her into a hug, and the two held onto each other for a moment before breaking away.

"Thank you so much, Courtney. You have no clue how much I'm going to wear this," Max said.

"Merry Christmas, Max."

"Merry Christmas, Courtney."

The two smiled as Courtney waved goodbye, walking back over to Victoria, Max gingerly setting the sweater back in the box and closing it.

She had half forgotten about Dana and her gift, until—

"Oh my God, Juliet, you have to see this!"

 _ **Fuck.**_

She saw it.

What did she think?

"Holy shit Dana, this is awesome."

That was good.

Max wasn't sure what to do or where to go. She was tempted to hide in her room. She had gotten her gift from Courtney, and Dana clearly saw her gift. She could just hide in her room and wait to see Kate and what she got later. Dana never had to know this was from her. Max could just… hide her feelings and let Dana have a nice, sweet gift and not have to worry about it.

She walked over to the tree as nonchalantly as possible, pretending to examine one of the ornaments closely, and hoping to listen in on Dana and Juliet. She was way too nervous to try and look over to see a reaction— they would definitely catch her and know it was her. As stealthily and low-key as possible, Max walked away from the tree, box held tightly to her chest, and tiptoed back to her dorm room.

She couldn't do it, she couldn't talk to Dana about how she felt. Nope, not at all. She had been more than brave enough for the whole year back in October, she could give herself the day off. Max was a bit disappointed in herself, but she just couldn't do it. Not with the whole situation. She'd go back to her dorm and just sleep the rest of the day.

Finals were done and she had given her crush a big gift she worked weeks on, she earned that much, at least.

As Max walked into her room, she peeked out her door, waving shyly to Kate, and seeing Courtney and Taylor standing next to Dana. She was showing that scrapbook to everyone. She… she must have really liked it.

Feeling as if she was on cloud nine— though with a swirl of anxiety in the pit of her stomach. She slowly walked over to her bed and fell down on, legs dangling off, closing her eyes.

What felt like mere minutes later, but was actually a couple of hours, Max was jolted awake by the sound of knocking on her door. She yawned and rubbed her eyes, pushing herself up off the bed.

"One second!" she called with a tired sigh.

She walked over to the door and opened it, seeing the last person she expected to see.

Dana.

Max's eyes were wide and her face bright red. Dana Ward was standing there, looking as great as ever, holding the scrapbook Max had made for her in her arms.

Fuck.

"Hey Max, can I come in?" Dana asked, sweet as always.

"O-Oh, yeah, come in," she stuttered out, moving out of the way, Dana walking in. Max slowly and shakily closed the door and turned to face her.

"You can— You can sit if you want," Max said, motioning to the bed. The two girls both walked over to Max's bed and sat down next to each other, which just set Max on edge even more. Dana, on the other hand, was as composed and calm as ever.

There was a brief silence between the two before Dana, as Max expected— and hoped— spoke up.

"Thanks for the scrapbook, it's… really amazing," Dana told her. Max had a small smile on her face, but more noticeably, was bright, bright red.

"Oh, but I didn't—"

"Save it, Max," Dana started, smiling at her.

"First of all, besides Victoria, no one is as good a photographer as you. Second of all, even if she's nicer now, Victoria would never do something like this," she added.

"Oh…"

"Plus, when I figured it was you but wasn't completely sure, I asked Kate and she told me it was you," Dana said. Max scrunched her eyes shut, feeling completely and utterly embarrassed.

"Yeah, I made it," Max admitted with a sigh. Dana quirked an eyebrow at Max, who she could easily tell was upset.

"Why are you so upset about it though? It's so great, I love it."

Max opened her eyes and looked at Dana.

"Really, like… you really do?"

"Yeah."

"You don't think, like, it's too sappy or corny?"

"No, it's so great. You got all these great pictures of me and it's decorated all great. Max, it's easily one of the best gifts I've ever gotten," she told her, wrapping an arm around the smaller brunette, pulling her in for a half hug.

"Oh… thanks, that means a lot. I just— I wanted to do something really great for you and—"

Max gulped hard. She had almost said how much she liked Dana. She dodged a bullet, just barely.

"What?"

No no no, she didn't just ask. Max felt weak. She felt like she was going to be sick.

"It's nothing, Dana…" she said quietly. Dana frowned, obviously concerned.

"Max, is everything ok? Come on, I don't want you to be upset…"

"I can… you won't get upset or flip out if I say something, will you?" Max asked, looking at Dana. Dana was taken aback, obviously very confused by what Max had said.

"Yeah… Max, are you sure everything's ok?"

"I just… look, one of the big reasons I made that scrapbook and spent weeks making it perfect was because I… I really like you," she choked out, letting out a breath after. It was finally out there. She probably fucked everything up, but it was out there.

Max definitely wasn't feeling any better after the fact, though.

Dana, on the other hand, was now red, and far less composed than she had been. Her eyes wide and her mouth open in surprise. It was the last thing Dana had ever expected to hear from the hipster.

"Really?"

"Yeah— and I'm so sorry I told you, Dana. I've just been stressed and I've been going back and forth on whether or not to tell you," Max explained, Dana nodding slowly.

"I know you're dating Trevor, I know. And I feel so awful about liking you, let alone even just telling you right now. I really do and I'm really sorry," she continued, sighing.

"Max."

"You're way cooler than me. You're the head cheerleader at Blackwell Academy, and I'm just Max Caulfield."

"Max."

"And I just—"

"Max!"

Max stopped going on and on and froze, looking over at Dana.

"Sorry…"

"Max, you don't have to be sorry about how you feel," Dana assured her, with a warm smile on her face.

"Are you sure…?" she asked. She knew Dana was sincere judging by her voice and expression, but she just had to make sure.

"Positive."

"Thanks… you— you really don't mind how I feel about you? I… I don't think I can just turn my feelings off," Max sighed. She wished she could, but they both knew it wasn't that easy.

"It's fine, really. I'm flattered, even. I know you think you're some dork or loser, you aren't. You're kind and sweet and far greater than you think you are," Dana told her. Max felt like she was dreaming. One of the coolest girls at Blackwell giving her all these compliments?

She was going to wake up at any moment.

"And plus, with Trevor… we've been sorta… rocky, lately," Dana admitted, glancing off to the side.

"O-Oh, I'm sorry Dana," Max said sincerely. Even if she was crushing on her, she didn't want Dana's relationship to be awful.

"It's fine, just, we've been going back and forth if our relationship is right and we're just not sure," she shrugged, like it was nothing.

Though even Max could tell it wasn't exactly the easiest thing for Dana to talk about right now.

"So in the mean time… if you ever want to hang out, just text me," Dana suggested, a small smile on her face. Max offered a smile back, hoping it would help the other feel better.

"I'd really like that. Just, we can hang out and have fun, nothing big," Max said, and Dana nodded.

"That'd be fun, Max."

The two stayed silent for a moment, both a bit red. Max knew it wasn't exactly a date with Dana, but it would be nice. Even hanging out with Dana would be something that Max would love.

She just wanted to hang out with her more, get to know her better— at this point in time even help her feel better about what she was going through.

"…I should get going. Juliet and I are gonna grab dinner soon," Dana said. Max was doing her best to hide a frown.

"Oh, ok, I'll see you later, Dana," she said, looking at the cheerleader, who was still sitting next to her on the bed.

She offered up another kind smile, and Dana smiled back. Hopefully it was helping her feel better.

"Thanks again for the gift Max, I'm going to love it forever," Dana told her one last time. She was happy she did such a good job with her gift for her crush.

But Max didn't expect it when Dana leaned in and kissed her on the cheek. Enough to be felt, but soft and sweet.

By the time she realized it, Dana had pulled away and started to head to the door. Max however, was bright red, and felt like she was going to scream from what just happened.

"Merry Christmas, Max."


End file.
